Sulfonation, benzoic acid phenol

Sulfonate ester, formation from sulfonyl chloride and alcohol, 67, 78, 84, 145 Sulfonation, benzoic acid, 269 phenol, 104 o-xylene, 47... 

The cumene oxidation route is the lea ding commercial process of synthetic phenol production, accounting for more than 95% of phenol produced in the world. The remainder of synthetic phenol is produced by the toluene oxidation route via benzoic acid. Other processes including benzene via cyclohexane, benzene sulfonation, benzene chlorination, and benzene oxychl orin ation have also been used in the manufacture of phenol. A Hst of U.S. phenol production plants and their estimated capacities in 1994 are shown in Table 2, and worldwide plants and capacities are shown in Table 3. 

Kennedy and Stock reported the first use of Oxone for many common oxidation reactions such as formation of benzoic acid from toluene and of benzaldehyde, of ben-zophenone from diphenyhnethane, of frawi-cyclohexanediol Ifom cyclohexene, of acetone from 2-propanol, of hydroquinone from phenol, of e-caprolactone from cyclohexanone, of pyrocatechol from salicylaldehyde, of p-dinitrosobenzene from p-phenylenediamine, of phenylacetic acid from 2-phenethylamine, of dodecylsulfonic acid from dodecyl mercaptan, of diphenyl sulfone from diphenyl sulfide, of triphenylphosphine oxide from triphenylphosphine, of iodoxy benzene from iodobenzene, of benzyl chloride from toluene using NaCl and Oxone and bromination of 2-octene using KBr and Oxone . Thus, they... 

Before 1970, there were five different processes used to make phenol in the United States the sulfonation route, chlorobenzene hydrolysis, the Raschig process, cumene oxidation, and the benzoic acid route. By 1978, the first three processes had essentially disappeared, and 98 percent of the remaining plant capacity was based on cumene oxidation. The oxidation process is shown in Fig. 10.33. 

On bromination of o- or /7-hydroxy- or o- or /7-amino-benzoic acid, or the corresponding sulfonic acids, even at room temperature, bromine replaces the COOH or S03H group with liberation of C02 or H2S04 as the case may be. At 40-45° the CHO group of o- or /7-hydroxy- or o- or /7-aminobenzaldehyde is also replaced by bromine, with evolution of CO. The end products are 2,4,6-tribromo-phenol or -aniline.460 Thus /7-hydroxybenzoic and sulfanilic acid, for example, can be determined quantitatively by means of O.lN-bromide-bromate solution. 

Polynaphthylimide with iV-naphthylimide orfho-sutetituents was prepared by the reaction of 3,3 -diamino-4,4 -di(p-aminophenoxy) diphenyl sulfone [164] with an equimolar amount of bis(naphthalic anhydride) followed by treatment with a two-fold molar amount of naphthalic anhydride in a m-cr ol-benzoic acid medium under the conditions of high-temperature catalytic polycondensation. The polymer was soluble in phenolic, amide solvents as well as in tetrachloroethane its molecular mass was of the order of 60 000, the softening temperature 340 °C and the temperature of 10 % mass loss 480 °C (Table 16). 

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